Stereoselective synthesis of the gamma-lactam hydrolysate of the thiopeptide cyclothiazomycin |
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Authors: | Bagley Mark C Xiong Xin |
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Institution: | School of Chemistry, Cardiff University, P.O. Box 912, Cardiff, CF10 3TB, UK. bagleymc@cf.ac.uk |
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Abstract: | reaction: see text] Bohlmann-Rahtz pyridine synthesis of a chiral nonracemic enamine and thiazolylpropynone gives a terminal-protected pyridine-containing gamma-amino acid in high optical purity in a sequential one-pot multicomponent reaction that proceeds with total control of regiochemistry and with minimal racemization. Further elaboration has established the synthesis of the gamma-lactam acidic hydrolysate of the macrocyclic thiopeptide antibiotic cyclothiazomycin, a selective renin inhibitor, in only four steps and 30% overall yield and has confirmed its structure. |
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